3-methyl-4-piperidine-4-yl-benzonitrile | 1013025-85-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 3-methyl-4-piperidine-4-yl-benzonitrile
• 英文别名: 3-Methyl-4-piperidin-4-ylbenzonitrile
• CAS: 1013025-85-8
• 化学式: C₁₃H₁₆N₂
• 分子量: 200.283
• InChiKey: FCPUDUJADYXUEZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  35.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  dimethyl 4-[(chlorosulfonyl)methyl]piperidine-1,4-dicarboxylate 、 3-methyl-4-piperidine-4-yl-benzonitrile 在 N,N-二异丙基乙胺 作用下， 以88%的产率得到
  参考文献：
  名称：

  Conversion of an MMP-potent scaffold to an MMP-selective HER-2 sheddase inhibitor via scaffold hybridization and subtle permutations

  摘要：

  A series of beta-sulfonamide piperidine hydroxamates were prepared and shown to be potent inhibitors of the human epidermal growth factor receptor-2 (HER-2) sheddase with excellent selectivity against MMP-1, -2, -3, and -9. This was achieved by exploiting subtle differences within the otherwise highly conserved S-1' binding pocket of the active sites within the metalloprotease family. In addition, it was discovered that the introduction of polarity to the P-1 and P-1' groups reduced the projected human clearance. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2007.11.086
• 作为产物：
  描述：

  Tert-butyl 4-(4-cyano-2-methylphenyl)piperidine-1-carboxylate 在 盐酸 作用下， 以 1,4-二氧六环 、 乙酸乙酯 为溶剂， 以100%的产率得到3-methyl-4-piperidine-4-yl-benzonitrile
  参考文献：
  名称：

  Conversion of an MMP-potent scaffold to an MMP-selective HER-2 sheddase inhibitor via scaffold hybridization and subtle permutations

  摘要：

  A series of beta-sulfonamide piperidine hydroxamates were prepared and shown to be potent inhibitors of the human epidermal growth factor receptor-2 (HER-2) sheddase with excellent selectivity against MMP-1, -2, -3, and -9. This was achieved by exploiting subtle differences within the otherwise highly conserved S-1' binding pocket of the active sites within the metalloprotease family. In addition, it was discovered that the introduction of polarity to the P-1 and P-1' groups reduced the projected human clearance. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2007.11.086

文献信息

• SUBSTITUTED CYCLIC HYDROXAMATES AS INHIBITORS OF MATRIX METALLOPROTEINASES
  申请人：Li Yun-Long

  公开号：US20110224189A1

  公开（公告）日：2011-09-15

  The present invention provides compounds of the formula: its enantiomers, diastereomers, racemic mixtures thereof, prodrugs, crystalline forms, non-crystalline forms, amorphous forms thereof, solvates thereof, metabolites thereof, and pharmaceutically acceptable salts, wherein the ring A substituent groups are fully defined in the following disclosure. The compounds of formula are inhibitors of metalloproteases such as matrix metalloproteases and sheddases, and are useful in treating diseases such as rheumatoid arthritis, psoriasis, neoplastic diseases, allergies and all those diseases wherein inhibition of MMPs is desirable.

  本发明提供了化合物的公式：其对映异构体，对映体混合物，前药，晶体形式，非晶体形式，无定形形式，其溶剂化物，代谢产物以及药学上可接受的盐，其中环A的取代基在以下披露中完全定义。公式化合物是金属蛋白酶抑制剂，例如基质金属蛋白酶和剪切酶，并且在治疗风湿性关节炎，牛皮癣，肿瘤性疾病，过敏和所有需要抑制MMP的疾病中有用。
• US7973041B2
  申请人：——

  公开号：US7973041B2

  公开（公告）日：2011-07-05
• [EN] HYDROXAMIC ACID DERIVATIVES AS METALLOPROTEASE INHIBITORS<br/>[FR] DERIVES D'ACIDE HYDROXAMIQUE EN TANT QU'INHIBITEURS DE METALLOPROTEASES
  申请人：INCYTE CORP

  公开号：WO2005117882A2

  公开（公告）日：2005-12-15

  The present invention provides compounds of Formula (I ) or (II), salt form or prodrug thereof, wherein variables are defined herein, that are modulators of metalloproteases such as matrix metalloproteases (MMPs) and ADAMs. The compounds or compositions described herein can be used to treat diseases associated with metalloprotease activity including, for example, arthritis, cancer, cardiovascular disorders, skin disorders, inflammation or allergic conditions.
• Conversion of an MMP-potent scaffold to an MMP-selective HER-2 sheddase inhibitor via scaffold hybridization and subtle permutations
  作者：David M. Burns、Chunhong He、Yanlong Li、Peggy Scherle、Xiangdong Liu、Cindy A. Marando、Mayanne B. Covington、Gengjie Yang、Max Pan、Sharon Turner、Jordan S. Fridman、Gregory Hollis、Kris Vaddi、Swamy Yeleswaram、Robert Newton、Steve Friedman、Brian Metcalf、Wenqing Yao

  DOI：10.1016/j.bmcl.2007.11.086

  日期：2008.1

  A series of beta-sulfonamide piperidine hydroxamates were prepared and shown to be potent inhibitors of the human epidermal growth factor receptor-2 (HER-2) sheddase with excellent selectivity against MMP-1, -2, -3, and -9. This was achieved by exploiting subtle differences within the otherwise highly conserved S-1' binding pocket of the active sites within the metalloprotease family. In addition, it was discovered that the introduction of polarity to the P-1 and P-1' groups reduced the projected human clearance. Published by Elsevier Ltd.